1,2-Dichloroethane → 2-cyclohexylmethyl-N-{1-[(5-ethyl-[1,3,4]oxadiazol-2-yl)-hydroxy-methyl]-butyl}-4-morpholin-4-yl-4-oxo-butyramide

HRID 1830194Notes

Reaction equation

HRID 1830194 reaction equation
[CH:1]1([CH2:7][CH:8]([CH2:12][C:13]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)=[O:14])[C:9]([OH:11])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.[NH2:22][CH:23]([CH2:33][CH2:34][CH3:35])[CH:24]([C:26]1[O:27][C:28]([CH2:31][CH3:32])=[N:29][N:30]=1)[OH:25].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.CN1CCOCC1>C(Cl)Cl>[CH:1]1([CH2:7][CH:8]([CH2:12][C:13]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)=[O:14])[C:9]([NH:22][CH:23]([CH:24]([C:26]2[O:27][C:28]([CH2:31][CH3:32])=[N:29][N:30]=2)[OH:25])[CH2:33][CH2:34][CH3:35])=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 218998342-Cyclohexylmethyl-4-morpholin-4-yl-4-oxobutyric acidHCID 694340542-amino-1-(5-ethyl-1,3,4-oxadiazole-2-yl)-1-pentanol HCl salt

Product 1

HCID 220540862-cyclohexylmethyl-N-{1-[(5-ethyl-[1,3,4]oxadiazol-2-yl)-hydroxy-methyl]-butyl}-4-morpholin-4-yl-4-oxo-butyramideYield 102.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of 2-cyclohexylmethyl-4-morpholin-4-yl-4-oxo-butyric acid (84.9 mg, 0.3 mmol), 2-amino-1-(5-ethyl-1,3,4-oxadiazole-2-yl)-1-pentanol HCl salt (70.5 mg), prepared as in reference 21, and HOBt (55.1 mg, 0.36 mmol) in MeCl2 (5 ml), was added EDC (86.4 mg, 0.45 mmol) and N-methylmorpholine (0.25 ml) at room temperature. After stirring for 14 hours, the reaction mixture was extracted with ethyl acetate. The organic layer was washed with saturated NaHCO3, brine, dried with MgSO4 and concentrated to yield 142 mg of 2-cyclohexylmethyl-N-{1-[(5-ethyl-[1,3,4]oxadiazol-2-yl)-hydroxy-methyl]-butyl}-4-morpholin-4-yl-4-oxo-butyramide; MS: 463.5(M−1), 465.3(M+1).

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated NaHCO3, brine
  3. dry with materialdried with MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-636e252479d14ff9b7d145286eab454b
Source dataset
uspto-grants-2006_06
Patent number
US07064123B1

Reaction notes

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